Thermally and/or photochemically crosslinked electroactive polymers in the manufacture of opto-electronic devices

Abstract

Preparation of thermally and/or photochemically crosslinkable oligomeric precursors and the use of those oligomeric precursors in preparing crosslinked electroactive polymers are described. The oligomers, polymers, and synthetic methods find utility in the manufacture of opto-electronic devices such as light emitting diodes, photoconductors, photovoltaic cells, and the like, wherein synthesis of electroactive films and polymeric multilayers is required.

What is claimed is: 
     
       1. An opto-electronic device comprising a substrate having a plurality of polymeric layers on the surface thereof, wherein at least one of the polymeric layers comprises a crosslinked electroactive polymer prepared by the process comprising: (a) reacting, under coupling conditions, (i) an initial oligomeric moiety comprised of arylene monomer units and bearing halo-substituted termini with (ii) a halobenzene reactant, wherein either the initial oligomeric moiety or the halobenzene reactant, or both the initial oligomeric moiety and the halobenzene reactant are substituted with a reactive group R containing an unsaturated bond, to produce a crosslinkable oligomer, and (b) crosslinking the crosslinkable oligomer under conditions sufficient to promote crosslinking.   
     
     
       2. The opto-electronic device of claim 1, comprising a light-emitting diode. 
     
     
       3. The opto-electronic device of claim 1, comprising a photovoltaic cell or detector. 
     
     
       4. The opto-electronic device of claim 1, comprising a photoconductor. 
     
     
       5. The opto-electronic device of claim 1, wherein the step (a) is carried out in the presence of a catalyst. 
     
     
       6. The opto-electronic device of claim 5, wherein the catalyst is a nickel catalyst. 
     
     
       7. The opto-electronic device of claim 6, wherein the catalyst is bis(1,5-cyclooctadiene)nickel. 
     
     
       8. The opto-electronic device of claim 5, wherein the initial oligomeric moiety has the structure   Hal.brket open-st.Y.brket close-st.Hal     wherein Hal represents a halogen atom, --[Y]-- comprises j monomer units --[X]-- and q monomer units --[X(R)]-- in which X comprises an arylene moiety, j and q are independently integers in the range of 0 to 50, and the sum of j and q is in the range of 1 to 50.   
     
     
       9. The opto-electronic device of claim 8, wherein X comprises a fluorescent moiety. 
     
     
       10. The opto-electronic device of claim 8, wherein X comprises an electron deficient moiety. 
     
     
       11. The opto-electronic device of claim 8, wherein X comprises an arylamine. 
     
     
       12. The opto-electronic device of claim 8, wherein X comprises an azo dye. 
     
     
       13. The opto-electronic device of claim 8, wherein the initial oligomeric moiety has the structure ##STR7## and the halobenzene reactant has the structure ##STR8## wherein p is an integer in the range of 1 to 50, and n is 1, 2, 3 or 4. 
     
     
       14. The opto-electronic device of claim 13, wherein Hal is bromo or chloro and n is 1. 
     
     
       15. The opto-electronic device of claim 14, wherein R is selected from the group consisting of ethenyl, ethynl, phenylethenyl, phenylethynyl, lower alkyl-substituted ethenyl, lower alkyl-substituted ethynyl, acrylate, ##STR9## wherein alk represents a lower alkyl substituent. 
     
     
       16. The opto-electronic device of claim 5, wherein step (c) is carried out by heating the oligomer. 
     
     
       17. The opto-electronic device of claim 5, wherein step (c) is carried out photochemically.